A common problem for healthcare providers is accurately tracking patients’ adherence to medication and providing real-time feedback on the management of their medication regimen. This is a particular problem for eye drop medications, as the current commercially available monitors focus on measuring adherence to pills, and not to eye drops. This work presents an intelligent bottle sleeve that slides onto a prescription eye drop medication bottle. The intelligent sleeve is capable of detecting eye drop use, measuring fluid level, and sending use information to a healthcare team to facilitate intervention. The electronics embedded into the sleeve measure fluid level, dropper orientation, the state of the dropper top (on/off), and rates of angular motion during an application. The sleeve was tested with ten patients (age ≥65) and successfully identified and timestamped 94% of use events. On-board processing enabled event detection and the measurement of fluid levels at a 0.4 mL resolution. These data were communicated to the healthcare team using Bluetooth and Wi-Fi in real-time, enabling rapid feedback to the subject. The healthcare team can therefore monitor a log of medication use behavior to make informed decisions on treatment or support for the patient.